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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Dudley vacation rentals

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AED 463
AED 711 total
includes taxes & fees
27 Sep - 28 Sep
The Tree House at Underhill Hollow
Exterior

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is AED 463
AED 690 total
includes taxes & fees
27 Sep - 28 Sep
Wizard's Roost at Underhill Hollow
Interior

3. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is AED 349
AED 673 total
includes taxes & fees
4 Oct - 5 Oct
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Property grounds

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
27 Sep - 28 Sep
SteamPunk Bunk House and Intergalactic Way Station
Exterior

5. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is AED 456
AED 809 total
includes taxes & fees
27 Sep - 28 Sep
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

6. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is AED 645
AED 914 total
includes taxes & fees
27 Sep - 28 Sep
Dove Cabin up in the Trees
1 bedroom, iron/ironing board, travel crib, WiFi (free)

7. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is AED 918
AED 1,341 total
includes taxes & fees
27 Sep - 28 Sep
Rustic Farmette Studio with Hot Tub & Pool
Property grounds

8. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is AED 311
AED 854 total
includes taxes & fees
27 Sep - 28 Sep
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

9. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is AED 349
AED 472 total
includes taxes & fees
27 Sep - 28 Sep
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Terrace/patio

10. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is AED 455
AED 1,125 total
includes taxes & fees
28 Sep - 29 Sep
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior

11. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is AED 551
AED 1,108 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Living area

12. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is AED 294
AED 421 total
includes taxes & fees
27 Sep - 28 Sep
Clean & Cozy Private-3 floor_R 2
Property grounds

13. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is AED 1,837
AED 2,314 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Iron/ironing board, WiFi, bed sheets

14. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
The price is AED 628
AED 858 total
includes taxes & fees
27 Sep - 28 Sep
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Outdoor dining

15. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior detail

16. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is AED 900
AED 1,108 total
includes taxes & fees
27 Sep - 28 Sep
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

17. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is AED 573
AED 1,155 total
includes taxes & fees
30 Sep - 1 Oct
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Smart TV

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is AED 821
AED 1,684 total
includes taxes & fees
6 Oct - 7 Oct
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Property grounds

19. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (9 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is AED 582
AED 732 total
includes taxes & fees
28 Sep - 29 Sep
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
TV

20. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is AED 551
AED 1,114 total
includes taxes & fees
28 Sep - 29 Sep
Large 3BD 1st Floor Apartment Minutes from 290
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dudley Hotel Reviews

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

10/10 Excellent
"Everyone was super nice super helpful. It was a great experience."
Joshua 5-night trip
Posted 16 hours ago
Hilton Garden Inn Worcester

Frequently asked questions

Are there vacation rentals in Dudley?

Yes, there are vacation rentals near popular attractions in Dudley, or you can choose a more remote option if you're looking for a relaxing stay. Dudley is known for its restaurants.

What's the top vacation rental that Dudley has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: Visitors like this Dudley vacation home rental. It is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Dudley?

Choose from 3 Expedia vacation rentals in Dudley for a memorable vacation.

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to get outside and enjoy nature. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a vacation rental in Dudley like?

Vacation rentals are private properties you can book for a long or short time in Dudley. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.